N-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)naphthalene-2-sulfonamide | 1034266-32-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)naphthalene-2-sulfonamide
• 英文别名: N-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]naphthalene-2-sulfonamide
• CAS: 1034266-32-4
• 化学式: C₂₄H₂₉N₃O₃S
• 分子量: 439.579
• InChiKey: YRVKJIDCHIEELY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-萘磺酰氯 、 1-(3-氨基)-4-(2-甲氧基苯基)哌嗪 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 生成 N-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)naphthalene-2-sulfonamide
  参考文献：
  名称：

  Synthesis and in vitro binding studies of piperazine-alkyl-naphthamides: Impact of homology and sulphonamide/carboxamide bioisosteric replacement on the affinity for 5-HT1A, α2A, D4.2, D3 and D2L receptors

  摘要：

  A series of carboxamide and sulphonamide alkyl(ethyl to hexyl) piperazine analogues were prepared and tested for their affinity to bind to a range of receptors potentially involved in psychiatric disorders. These chemical modifications led us to explore the impact of homology and bioisosteric replacement of the amide group. All of these compounds possessed a high affinity for 5-HT1A receptors, irrespective of the size of the linker, the carboxamide derivative with a pentyl linker had the highest affinity for alpha(2A) receptor sites and also a high affinity for 5-HT1A and D3 receptors. The sulphonamide analogue with a hexyl linker possessed a high affinity for 5-HT1A, D4.2 and D3 receptors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.002

文献信息

• Preparation of piperazine derivatives as 5-HT7 receptor antagonists
  作者：Juhee Yoon、Eun A Yoo、Ji-Yeon Kim、Ae Nim Pae、Hyewhon Rhim、Woo-Kyu Park、Jae Yang Kong、Hea-Young Park Choo

  DOI：10.1016/j.bmc.2008.04.023

  日期：2008.5

  Twenty-four compounds of 4-methoxy-N-[3-(4-substituted phenyl-piperazine-1-yl)propyl] benzene sulfonamides and N-[3-(4-substituted phenyl-piperazine-1-yl)propyl] naphthyl sulfonamides were prepared and evaluated as 5-HT(7) receptor antagonists. Most of the compounds showed the IC(50) values of 12-580nM. Four methyl branched analogues were also obtained, but the activity for methyl branched analogues

  4-甲氧基-N- [3-（4-取代的苯基-哌嗪-1-基）丙基]苯磺酰胺和N- [3-（4-取代的苯基-哌嗪-1-基）丙基]二十四种化合物萘磺酰胺被制备并评估为5-HT（7）受体拮抗剂。大多数化合物的IC（50）值为12-580nM。还获得了四个甲基支链类似物，但是对于甲基支链类似物的活性几乎与其直链同源物相同。在合成的化合物中，3c对5-HT（7）受体具有良好的活性，对5-HT（1a），5-HT（2a），5-HT（2c）和5-HT（6）具有良好的选择性）受体。
• Synthesis and in vitro binding studies of piperazine-alkyl-naphthamides: Impact of homology and sulphonamide/carboxamide bioisosteric replacement on the affinity for 5-HT1A, α2A, D4.2, D3 and D2L receptors
  作者：Mélissa Résimont、Jean-François Liégeois

  DOI：10.1016/j.bmcl.2010.07.002

  日期：2010.9

  A series of carboxamide and sulphonamide alkyl(ethyl to hexyl) piperazine analogues were prepared and tested for their affinity to bind to a range of receptors potentially involved in psychiatric disorders. These chemical modifications led us to explore the impact of homology and bioisosteric replacement of the amide group. All of these compounds possessed a high affinity for 5-HT1A receptors, irrespective of the size of the linker, the carboxamide derivative with a pentyl linker had the highest affinity for alpha(2A) receptor sites and also a high affinity for 5-HT1A and D3 receptors. The sulphonamide analogue with a hexyl linker possessed a high affinity for 5-HT1A, D4.2 and D3 receptors. (C) 2010 Elsevier Ltd. All rights reserved.